The measure of a “supermodel”–as established in the 1990s–used to be: A) Do you know them by their first name only? and B) Have they appeared in a George Michael video? It was a simpler time, for sure, but few would argue it was better.

Even then, the biggest (first) names of the era–your Kates, your Cindys, your Imans–understood that they were building brands, not just cultivating celebrity. As they began using their status to construct mini-empires, they inspired the next wave of models to think outside the runway. Check out the slideshow above to find out more.